- David Letterman (Self - Host)
- Paul Shaffer (Self -Musical Director)
- Alan Kalter (Self - Announcer (voice))
Episode: Charlie Sheen, John Mayer
Air Date: 2003-10-10
During CBS Mailbag, Alan has an awkward reunion with the first girl that ever kissed him, and "Ah-nuld" (Gerard) has an enlightened conversation with Dave. Later, Charlie Sheen promotes "Two and a Half Men."